Ethyl alpha-oxobenzenebutanoate → HCID 70393826, compound

HRID 1383102Notes

Reaction equation

HRID 1383102 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@H:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12][N:6]2[C:5](=[O:20])[CH2:4][CH2:3]1.O=[C:22]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C.[Pd]>[CH2:26]([O:25][C:23]([C@H:22]([NH:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@H:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11][CH2:12][N:6]2[C:5](=[O:20])[CH2:4][CH2:3]1)[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27].[CH2:26]([O:25][C:23]([C@@H:22]([NH:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@H:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11][CH2:12][N:6]2[C:5](=[O:20])[CH2:4][CH2:3]1)[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27]

Participants

6

Reactant 2

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 70393503HCID 70393503, compound

Product 2

HCID 70393826HCID 70393826, compoundHCID 70393860HCID 70393860, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.15 g of tert.butyl 8(S)-amino-2,3,6,7,8,9-hexahydro-5,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]diazepine-1(S)-carboxylate and 3.10 g of ethyl 2-oxo-4-phenylbutanoate in 50 ml of ethanol was hydrogenated over 1.0 g of 10% palladium-on-carbon in the presence of molecular sieve at 4 atmospheres for 48 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel to give 0.18 g of tert.butyl 8(S)-[1(R)-ethoxycarbonyl-3-phenylpropylamino]-2,3,6,7,8,9-hexahydro-5,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]diazepine-1(S)-carboxylate in the form of a pale yellow oil and subsequently 0.19 g of tert.butyl 8(S)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-2,3,6,7,8,9-hexahydro-5,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]diazepine-1(S)-carboxylate in the form of a pale yellow oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b9c96bcf26f44a0f9165c1b9c9867e8d
Source dataset
uspto-grants-1989_02
Patent number
US04808713

Reaction notes

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